CA2165206A1 - Preparation of Dimethyl Cyclohexanedicarboxylates - Google Patents

Preparation of Dimethyl Cyclohexanedicarboxylates

Info

Publication number
CA2165206A1
CA2165206A1 CA2165206A CA2165206A CA2165206A1 CA 2165206 A1 CA2165206 A1 CA 2165206A1 CA 2165206 A CA2165206 A CA 2165206A CA 2165206 A CA2165206 A CA 2165206A CA 2165206 A1 CA2165206 A1 CA 2165206A1
Authority
CA
Canada
Prior art keywords
preparation
dimethyl
cyclohexanedicarboxylates
catalysts
dimethyl cyclohexanedicarboxylates
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA2165206A
Other languages
French (fr)
Other versions
CA2165206C (en
Inventor
Bruce Leroy Gustafson
Yeong-Jen Kuo
Brent Alan Tennant
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Chemical Co
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2165206A1 publication Critical patent/CA2165206A1/en
Application granted granted Critical
Publication of CA2165206C publication Critical patent/CA2165206C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Disclosed is a process for the preparation of a dimethyl cyclohexanedicarboxylate by the hydrogenation of the analogous dimethyl benzenedicarboxylate ester in the presence of a class of palladium on alumina catalysts which have a unique combination of characteristics.
The use of the catalysts permits the process to be carried out at significantly lower process pressures.
CA002165206A 1993-06-15 1994-06-03 Preparation of dimethyl cyclohexanedicarboxylates Expired - Fee Related CA2165206C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/076,674 US5319129A (en) 1993-06-15 1993-06-15 Preparation of dimethyl cyclohexanedicarboxylates
US08/076,674 1993-06-15

Publications (2)

Publication Number Publication Date
CA2165206A1 true CA2165206A1 (en) 1994-12-22
CA2165206C CA2165206C (en) 1998-08-18

Family

ID=22133524

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002165206A Expired - Fee Related CA2165206C (en) 1993-06-15 1994-06-03 Preparation of dimethyl cyclohexanedicarboxylates

Country Status (11)

Country Link
US (1) US5319129A (en)
EP (1) EP0703895B1 (en)
JP (1) JP3499556B2 (en)
KR (1) KR100277245B1 (en)
CN (1) CN1042326C (en)
CA (1) CA2165206C (en)
DE (1) DE69410266T2 (en)
ES (1) ES2118418T3 (en)
SG (1) SG46408A1 (en)
TW (1) TW295582B (en)
WO (1) WO1994029259A1 (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI243188B (en) * 1997-12-19 2005-11-11 Basf Ag Hydrogenation of benzenepolycarboxylic acids or derivatives thereof using a catalyst containing macropores
DE19927978A1 (en) 1999-06-18 2000-12-21 Basf Ag New esters of cyclohexane-1,3- and -1,4-dicarboxylic acid, useful as toxicologically acceptable plasticizers, e.g. for PVC, obtained by hydrogenation of corresponding isophthalate and terephthalate esters
DE19939544C1 (en) 1999-08-20 2001-02-15 Haarmann & Reimer Gmbh Process for the preparation of methyl cyclohexyl propionate
DE10128242A1 (en) * 2001-06-11 2002-12-12 Basf Ag Hydrogenation of organic compounds e.g. aromatic amines or phenols, by using hydrogen in presence of catalyst comprising ruthenium on amorphous silicon dioxide based carrier
DE10146869A1 (en) 2001-09-24 2003-04-24 Oxeno Olefinchemie Gmbh Alicyclic polycarboxylic ester mixtures with a high trans content and process for their preparation
EP2045286B1 (en) * 2001-09-25 2013-04-24 ExxonMobil Chemical Patents Inc. Plasticised polyvinyl chloride
US6803341B2 (en) * 2002-01-18 2004-10-12 Chinese Petroleum Corporation Method of a high stability selectable hydrogenate catalyst producing and using for DMCHD manufacturing
GB0227087D0 (en) * 2002-11-20 2002-12-24 Exxonmobil Chem Patents Inc Hydrogenation of benzene polycarboxylic acids or derivatives thereof
GB0227086D0 (en) * 2002-11-20 2002-12-24 Exxonmobil Res & Eng Co Hydrogenation processes
DE102004063637A1 (en) 2004-12-31 2006-07-13 Oxeno Olefinchemie Gmbh Process for the preparation of alicyclic carboxylic acids or their derivatives
DE102004063673A1 (en) * 2004-12-31 2006-07-13 Oxeno Olefinchemie Gmbh Process for the continuous catalytic hydrogenation of hydrogenatable compounds on solid, fixed-bed catalysts with a hydrogen-containing gas
US7632962B2 (en) * 2006-04-26 2009-12-15 Eastman Chemical Company Hydrogenation process and catalysts
CN102796001A (en) * 2011-05-25 2012-11-28 江苏恒祥化工有限责任公司 Solvent-free preparation method of 1, 4-DMCD
TWI421240B (en) 2011-12-12 2014-01-01 Ind Tech Res Inst Process for hydrogenation of polycarboxylic acids or derivatives thereof
US9090553B2 (en) 2012-10-05 2015-07-28 Basf Se Process for preparing cyclohexanepolycarboxylic acid derivatives having a low proportion of by-products
EP2716623A1 (en) 2012-10-05 2014-04-09 Basf Se Method for the preparation of cyclohexane polycarboxylic acid derivatives with low proportion of by-product
TWI577658B (en) * 2015-05-06 2017-04-11 中國石油化學工業開發股份有限公司 Method for preparation of dimethyl 1,4-cyclohexanedicarboxylate and method for preparation of 1,4-cyclohexanedimethanol
CN105732370A (en) * 2016-01-28 2016-07-06 江苏清泉化学股份有限公司 Method for preparing dioctyl 1,4-cyclohexanedicarboxylate
US11673125B2 (en) 2016-08-18 2023-06-13 The University Of Chicago Metal oxide-supported earth-abundant metal catalysts for highly efficient organic transformations

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2675390A (en) * 1950-05-19 1954-04-13 Edgar F Rosenblatt Hydrogenation of cyclic-compounds
GB817736A (en) * 1955-08-26 1959-08-06 Chimiotherapie Lab Franc Esters of trans-hexahydroterephthalic acid and of the mono-acid chloride of trans-hexahydroterephthalic acid
US2794030A (en) * 1955-10-18 1957-05-28 Union Carbide & Carbon Corp Aliphatic esters of 4, 5-epoxycyclohexane-1, 2-dicarboxylic acids
US3027398A (en) * 1960-02-01 1962-03-27 Du Pont Process for preparing dimethyl 1, 4-cyclohexanedicarboxylate
DE1154096B (en) * 1962-02-23 1963-09-12 Witten Gmbh Chem Werke Process for the preparation of 1,4-cyclohexanedicarboxylic acid dialkyl esters
NL6405867A (en) * 1963-05-29 1964-11-30
US3334149A (en) * 1964-07-21 1967-08-01 Eastman Kodak Co Plural stage hydrogenation of dialkyl terephthalate using palladium and then copper chromite
US3444232A (en) * 1966-05-18 1969-05-13 Squibb & Sons Inc O-alkyl or phenylalkyl benzohydroxamic acids
US4024173A (en) * 1967-09-02 1977-05-17 Dynamit Nobel Aktiengesellschaft Process for the manufacture of cyclohexene dicarboxylic acid esters
US3824193A (en) * 1972-03-30 1974-07-16 Eastman Kodak Co Alkaline reactivation of alumina supported palladium catalysts
DE2823165A1 (en) * 1978-05-26 1979-11-29 Bayer Ag PROCESS FOR MANUFACTURING CYCLOALIPHATIC CARBONIC ACID ESTERS
JP2717265B2 (en) * 1988-06-03 1998-02-18 東都化成株式会社 Thermosetting resin composition

Also Published As

Publication number Publication date
DE69410266D1 (en) 1998-06-18
CN1042326C (en) 1999-03-03
JP3499556B2 (en) 2004-02-23
ES2118418T3 (en) 1998-09-16
US5319129A (en) 1994-06-07
JPH08511531A (en) 1996-12-03
SG46408A1 (en) 1998-02-20
CA2165206C (en) 1998-08-18
DE69410266T2 (en) 1998-09-10
CN1099382A (en) 1995-03-01
KR100277245B1 (en) 2001-02-01
KR960702827A (en) 1996-05-23
WO1994029259A1 (en) 1994-12-22
EP0703895A1 (en) 1996-04-03
EP0703895B1 (en) 1998-05-13
TW295582B (en) 1997-01-11

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Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20130604